Synthesis of Aryl-substituted Pyrrole Derivatives with Tunable Emissive Behaviors

doi:10.7517/issn.1674-0475.190101

Abstract

Abstract: A new class of pyrrole derivatives containing methyl benzoate groups, MB3PE2 and MB3, were synthesized using the Sonogashira coupling reaction, and were used to develop typical donor (D, pyrrole)-acceptor (A, -PhCOOCH₃) fluorophores that exhibited tunable fluorescent properties. Moreover, their emission properties and fluorescence dynamics were systematically investigated to elucidate their structure-property relationships. The results revealed that the π-conjugation and/or D-A geometry of these compounds has a significant effect on their emissive behaviors. MB3PE2 has π-T-shaped D-A structure while MB3 has T-shaped D-A structure. Both of them emit blue light with apparent solvatochromic effects but had different quantum yields in different states such as solution and aggregates states, which are more 2.6 times quantum yield of π-T-shaped D-A MB3PE2 than that of T-shaped MB3.The result provides a guidance for designing new D-A dyes with high quantum yield in solution.

Key words: solvatochromism, pyrrole, photoluminescence, quantum yield

GAO Yu, LIU Guogang, SHI Jianbing, DONG Yuping. Synthesis of Aryl-substituted Pyrrole Derivatives with Tunable Emissive Behaviors[J]. Imaging Science and Photochemistry, 2019, 37(2): 93-106.

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